Curing resin, method for producing same and curing resin composition

Abstract

An object of the present invention is to provide a curable resin having a silyl group at the terminal that is also moisture-hardening resin which has lower in viscosity when it is used and provides superior adhesiveness when it is utilized for adhesive, sealant, and paint. The object of the invention could be achieved by a curable resin that has silicon atom-containing groups having a silicon atom bound to one or more hydrolysable groups such as alkoxy groups, acetoxy groups and oxim groups at the ends of the molecule, thioether and hydroxyl groups in the molecule, and a polymer having a polyoxyalkylene, (meth)acrylic ester, or hydrocarbon polymer as the main chain skeleton.

Description

TECHNICAL FIELD[0001]The invention relates to a curable resin, a production method thereof, and a composition containing the curable resin, and in particular to a curable resin favorable for use in applications such as adhesive, sealant, and paint, a production method thereof, and a composition containing the curable resin exhibiting superior adhesiveness in such applications.BACKGROUND OF THE INVENTION[0002]The silylated urethane resins disclosed in U.S. Pat. Nos. 3,030,020 and 3,350,011, which are favorably adhesive to a wide variety of materials and environmentally friendly, are resins meeting the demands of the times and thus, resins of practical use in general adhesion applications. However, the silylated urethane resins are more viscous because of the urethane bonds contained therein, resulting in restriction on blending ratio of components for various adhesives and sealants. Further, the modified silicone resins having a polyoxyalkylene polymer as the main chain skeleton disc...

AI Technical Summary

Benefits of technology

[0100]The (co)polymerization of the compounds (d) and the (co)polymerization of the compounds (d) and (e) is particularly favorably conducted in the curable resin above, for increasing the advantageous effects of the present invention. The composition 1 according to the invention contains 100 parts by weight of the curable resin and 5 to 1,000 parts, preferably 10 to 100 parts, by weight of the polymer (C) prepared by polymerization of the compound (d). A content of the polymer (c) of less than 5 parts by weight may cause a problem of insufficient reinforcement by addition of the polymer (C), while a content of more than 1,000 parts by weight, of excessively high viscosity of the composition 1. The composition 2 according to the invention contains, in addition to the composition 1, the polymer of the compound (e) in an amount of 1 to 50 wt %, preferably 5 to 30 wt %, with respect to the total amount of the polymer (C) and the polymer of the compound (e). If the content of polymer formed from a compound (e) is less than 1 wt %, it is not effective in exhibiting the reinforcement effect by addition of the compound (e) polymer, while a content of more than 50 wt % causes a problem of excessively high viscosity of the composition 2.

[0101]The composition 3 according to the invention contains the curable resin described above and a curing catalyst for the curable resin (hereinafter, referred to as compound (f)). Addition of the compound (f) to the curable resin allows hardening of the curable resin and makes the composition 3 function as an adhesive, sealer, or the like.

[0102]Examples of the curing catalyst compounds (f) include basic substances such as organic tin compounds, metal complexes, amines; organic phosphoric acid compounds, water (moisture in air) and Lewis acids, and the like.

[0103]Examples of the organic tin compounds include dibutyltin dilaurate, dioctyltin dimalate, dibutyltin phthalate, stannous octoate, dibutyltin methoxide, dibutyltin diacetylacetate, dibutyltin diversatate, reaction products from dibutyltin oxide and aphthalic diester, dibutyltin oxide, dibutyltin distearate, dibutyltin dioctoate, dibutyltin dioleylmalate, dibutyltin dioctylthioglycolate, dibutyltin laurate oxide, dibutyltin diacetate, dibutyltin monoacetate, dibutyltin monoacetate, dibutyltin dimercaptopropionic acid octyl ester, dibutyltin monomalate, dibutyltin dimalate, stannous octoate, tin neodecanoate, tin stearate, and the like; as well as SCAT-46A, SCAT-4A, SCAT-9, SCAT-24, SCAT-52, SCAT-8, SCAT-8B, SCAT-1, SCAT-2L, SCAT-7, SCAT-27, SCAT-31A, SCAT-32A, and STANN JF-9B (tradename, manufactured by Sankyo Organic Chemicals Co., Ltd.), U-130, U-22, U-280, U-340, U-350, U-360, U-370, U-373, U-810, U-840, U-850, U-860, and U-870 (tradename, manufactured by Nitto Kasei Co., Ltd.), and the like.

[0104]In addition to the compounds above, the organic tin compounds include the following poly(dialkylstannoxane) dicarboxylates represented by General Formula 33.

[0106]In the General Formula (33), R20 and R21 each represent a substituted or unsubstituted hydrocarbon group having 1 to 12 carbon atoms; u is an integer of 1 or more; and R20 and R21 may be the same as or different from each other.

Problems solved by technology

However, the silylated urethane resins are more viscous because of the urethane bonds contained therein, resulting in restriction on blending ratio of components for various adhesives and sealants.

Further, the modified silicone resins having a polyoxyalkylene polymer as the main chain skeleton disclosed in Japanese Patent Application Laid-Open (JP-A) No. 08-337713 and others are less viscous, but not sufficiently adhesive because the resins do not have active hydrogen atoms in the molecular skeleton, and thus there exists a need for improvement in adhesiveness.

Further, silylated urethane resins having a (meth)acrylic ester polymer or a hydrocarbon polymer as the main chain skeleton are also known, but they are highly viscous, causing a problem in processability.

Furthermore, a curable epoxy compound containing hydroxyl groups and a thioether group in the molecule which is a reaction product from a hydrolysable silyl group-containing mercaptosilane and an epoxy compound, was described in JP-A No. 06-293784, but the curable epoxy compound is also highly viscous, causing the problem in processability.

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